Relevant Data

Food Additives Approved by WHO:

Flavouring Substances Approved by European Union:

  • Phenylacetaldehyde [show]

General Information

MaintermPHENYLACETALDEHYDE
Doc TypeASP
CAS Reg.No.(or other ID)122-78-1
Regnum 172.515

From www.fda.gov

Computed Descriptors

Download SDF
2D Structure
CID998
IUPAC Name2-phenylacetaldehyde
InChIInChI=1S/C8H8O/c9-7-6-8-4-2-1-3-5-8/h1-5,7H,6H2
InChI KeyDTUQWGWMVIHBKE-UHFFFAOYSA-N
Canonical SMILESC1=CC=C(C=C1)CC=O
Molecular FormulaC8H8O
Wikipediaphenylacetaldehyde

From Pubchem


Computed Properties

Property Name Property Value
Molecular Weight120.151
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count2
Complexity82.6
CACTVS Substructure Key Fingerprint A A A D c c B w I A A A A A A A A A A A A A A A A A A A A A A A A A A w A A A A A A A A A A A B A A A A G g A A A A A A D A C g m A I w A I A A A A C I A i h S g A A C A A A g A A A I i A E A A I g I I D K A F R C A I A A g g A A I i A c I i I C O A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area17.1
Monoisotopic Mass120.058
Exact Mass120.058
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count9
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

From Pubchem


Food Additives Biosynthesis/Degradation


ADMET Predicted Profile --- Classification

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9826
Human Intestinal AbsorptionHIA+0.9909
Caco-2 PermeabilityCaco2+0.9175
P-glycoprotein SubstrateNon-substrate0.8161
P-glycoprotein InhibitorNon-inhibitor0.9608
Non-inhibitor0.9868
Renal Organic Cation TransporterNon-inhibitor0.8610
Distribution
Subcellular localizationMitochondria0.5919
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8249
CYP450 2D6 SubstrateNon-substrate0.9402
CYP450 3A4 SubstrateNon-substrate0.8189
CYP450 1A2 InhibitorInhibitor0.5562
CYP450 2C9 InhibitorNon-inhibitor0.9404
CYP450 2D6 InhibitorNon-inhibitor0.9502
CYP450 2C19 InhibitorNon-inhibitor0.8683
CYP450 3A4 InhibitorNon-inhibitor0.9593
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7643
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8888
Non-inhibitor0.9741
AMES ToxicityNon AMES toxic0.9139
CarcinogensNon-carcinogens0.5626
Fish ToxicityHigh FHMT0.7072
Tetrahymena Pyriformis ToxicityHigh TPT0.9964
Honey Bee ToxicityHigh HBT0.7060
BiodegradationReady biodegradable0.6159
Acute Oral ToxicityIII0.9328
Carcinogenicity (Three-class)Non-required0.7290

From admetSAR


ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility-1.3239LogS
Caco-2 Permeability1.9770LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.8351LD50, mol/kg
Fish Toxicity0.3860pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.1622pIGC50, ug/L

From admetSAR


Toxicity Profile

Route of ExposureNone
Mechanism of ToxicityNone
MetabolismNone
Toxicity ValuesNone
Lethal DoseNone
Carcinogenicity (IARC Classification)Not listed by IARC.
Minimum Risk LevelNone
Health EffectsNone
TreatmentNone
Reference
  1. Cho IH, Kim SY, Choi HK, Kim YS: Characterization of aroma-active compounds in raw and cooked pine-mushrooms (Tricholoma matsutake Sing.). J Agric Food Chem. 2006 Aug 23;54(17):6332-5.[16910727 ]
  2. Sumner SJ, Fennell TR: Review of the metabolic fate of styrene. Crit Rev Toxicol. 1994;24 Suppl:S11-33.[7818768 ]
  3. Watson WP, Munter T, Golding BT: A new role for glutathione: protection of vitamin B12 from depletion by xenobiotics. Chem Res Toxicol. 2004 Dec;17(12):1562-7.[15606130 ]

From T3DB


Taxonomic Classification

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassPhenylacetaldehydes
Intermediate Tree NodesNot available
Direct ParentPhenylacetaldehydes
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsPhenylacetaldehyde - Alpha-hydrogen aldehyde - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aldehyde - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenylacetaldehydes. These are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde.

From ClassyFire


Targets

General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Tryptamine:oxygen oxidoreductase (deaminating) activity
Specific Function:
The enzyme prefers aromatic over aliphatic amines.
Gene Name:
tynA
Uniprot ID:
P46883
Molecular Weight:
84378.17 Da

From T3DB